


Sex and the Single Guy

by Harsley



Category: Shameless (US)
Genre: AU, Future Fic, M/M, Sex and the City AU, Writer!Ian
Language: English
Status: Completed
Published: 2014-09-26
Updated: 2014-09-26
Packaged: 2018-02-18 21:28:58
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,858
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2362724
Author URL: https://archiveofourown.org/users/Harsley/pseuds/Harsley
Summary: <blockquote class="userstuff">
              <p>Ian Gallagher writes a sex column for a popular New York City magazine. He meets his match in fresh off the boat, real estate developer Mickey Milkovich.</p>
            </blockquote>





	Sex and the Single Guy

**Author's Note:**

> Here's a fic that I wrote a few months ago. I barely edited it so any mistakes are mine.

“Ian Gallagher is Manhattan's new It Guy. His romance column is single-handedly helping revive print circulation of New York Today by making it a must-read for singles everywhere regardless of where you fall on the Kinsey spectrum. His sharp wit, heart breaking back story, and outrageous anecdotes about finding love in the Big Apple are a must read for any in-the-know metropolitan.”

Ian was fresh out of the shower when Fiona, called. She hadn't said hi or asked how he was. Instead, she launched into reading a blurb about him that someone allegedly important had written. She was proud to say the least – as she should be. If it wasn't for Fiona, God only knows where he'd be. Either in jail or married to some Southside skank like Karen Jackson. Instead, he was on his way to meet his best friend, Sam, for drinks.

“Where'd you find that?” Ian asks. 

“It was in Cosmo,” Fiona tells him.

“Since when do you read Cosmo?”

“Since I want to learn 69 new sex positions to drive my man cray.”

Unwittingly, an image of Jimmy-Steve and Fiona trying number 19 popped in his head and he almost gagged. “Yeah, okay, this conversation is over now.”

“Love, you. Call soon.”

“I will,” Ian promises as he hangs up. 

Talking to his family back in Chicago always had a way of bringing Ian back down to Earth. If he was still scraping for survival on the southside, he wouldn't give a fuck what he was wearing. Why should he be any different in New York? He picked out a simple long sleeve black shirt and his beat up leather jacket. He even took the subway.

“You're late,” Sam deadpans as Ian sits down.

“I took public transportation,” Ian reveals as if it's some dirty secret.

“Why?” 

“Reminds me of home.”

Sam Jones was in his mid thirties, owner of his own public relations firm, and the ultimate embodiment of New York City. He had been Ian's first major contact after graduating from New York University. They met when Sam walked up to Ian and pretended to be his boyfriend to avoid seeming alone when he ran into his ex. Afterward, Sam insisted he do Ian a favor. The favor landed Ian his first writing job and his first best friend in the city.

“If I were you, I would just try to block out that whole Chicago thing,” Sam was saying. The bar he had picked to meet in played the Best of the '90s and served cocktails in glasses the size of fish bowls. 

“Why are we here?” Ian wanted to know. “This isn't your usual hot spot.”

“I have a stalker.”

“Stalker?”

“Yes, the assistant of my new client keeps popping up everywhere I am. First, dinner with my Hermes connection. Thought it was a coincidence. Then, outside the baths. She looked like she had been waiting. Last night, she's on my block, walking her dog. I asked the client – she lives in Brooklyn...”

As Sam went on and on about how these straight girls were getting out of line nowadays, Ian noticed him. The first thing he noticed how short he was, at a least a head shorter than Ian's own towering height. Then the tailored Prada suit so obviously the guy had style. His thick hair was stylishly cut and slicked back and he was reaching down at that moment for a pack of cigarettes. Ian had never been so drawn to a guy in his life.

“Ian. Ian!” Sam snapped his fingers in his face.

“What?” Ian's eyes flickered to Sam then back to the man leaning over the bar.

“Do you hear anything about I was saying? The gummy bear in the baths?”

Confusion must have shown on Ian's face as he sipped from his fishbowl. Sam looked behind him, scanning the room. Ian, instantly terrified, grabbed his best friend's wrist. Of course, Sam Jones was never one to be deterred. When he finally found what he was looking for, he sank back in his seat and smiled at Ian mischievously.

“You were checking out that guy,” Sam accused.

“What guy?” Ian played dumb. 

“I know your type, Gallagher. The Marlboro man at the bar in last season's Prada. I'd suck his dick, too.”

“Surprised you haven't.”

To say Sam got around would be an understatement. He had single-handedly fucked his way through Manhattan island with little to no discretion. He enjoyed sex, condemned monogamy, and was blunt to the point of inappropriate. He strangely reminded Ian of home.

“I would but he's fresh off the boat,” Sam reveals.

“You know him?” Ian asks. Stupid question. It was Sam's job to know everybody.

“His name is Michael Milkovich. He's from Chicago and works in... real estate development.”

“Why'd you say it like that?” 

“Like what?”

“Like 'ellipsis real estate development'.”

“Ellipsis?”

“Dot, dot, dot.”

Sam looks around conspiratorially before leaning forward and saying softly to Ian. “There's a rumor he funded his first deal with drug money.”

“He's a drug dealer?”

“Just what I heard. Doubt it though. When have you ever seen a drug dealer wear couture?”

True enough. Then it again, it was New York City. Stranger things have happened. 

When Ian glanced over at the bar, he saw the brunet walking toward him. There must have been a hotter guy behind him or something. Apparently not, because he stopped right at Ian's table, the cigarette hanging out of his mouth.

“You got a light?” 

Ian fumbles with his jacket pocket and ended up knocking a short sleeve of Trojans out. Mortified, Ian tries to pick them up but the brunet's already reaching for them. He picks them up, unabashedly examining them. 

“Size large, huh?” 

Ian flushes as he lights the cigarette, embarrassed. And he's never embarrassed. Ian's not vain but he is aware that he's attractive if pale, alien looking redheads were your type. The way Milkovich's eyes were roaming his body, Ian thought that maybe they were. He took a long drag of his cigarette before his blue eyes found Ian's again. Smoke filtered out his mouth as he replied,

“Thanks for the light.”

With a half smile, the brunet walks out of the way and out of the bar. Ian watches him before turning back to Sam, a grin threatening to split his face. Sam only rolls his eyes and fishes out his phone.

“That just happened right?” Ian asks. “I didn't just dream that?”

“No, he was hot and totally into you,” Sam confirms, tapping and swiping away at his phone. 

“You think?”

“What smoker do you know is ever caught without a lighter?”

For the rest of the day, Ian couldn't get his mind of that Milkovich guy. Somehow the name Michael didn't fit with the image of that badass in a designer label. It was too... clean, too proper. What kind of real estate developer had an obscenity tattooed on his knuckles? Plus, the guy was from Chicago? Ian would bet anything he was southside. Ian found himself reaching for his phone, about to call his brother, Lip, to see if he recognized the name when his phone rang. He glanced at the screen and saw it was a number he didn't recognize. 

“Hello?” Ian answers. There's a beat of no answer. “Hello?”

“Is this Trojans, Size Large?”

Ian bit back a laugh. “I prefer Ian. Who may I ask is calling?”

There was a bit of nervous chuckling on the other end. “You gave me a light at that bar?”

“Oh. Tall black guy right? Forward for the Knicks?”

“It's Mickey, jerk off.”

“How'd you get my number?”

“Someone named Sam Jones called around and got my assistant. Said he'd have some information I'd be interested in.”

Sam worked quick. Their excursion had happened a little less than three hours before.

“You busy tonight?” Mickey was asking.

“It's Friday night in New York City. Of course I'm busy,” Ian told him.

“Don't tell me you're one of those dudes.”

“What is that supposed to mean, 'one of those dudes'?”

“The dudes who do nothing but go clubbing and workout and shit.”

“I happen to like clubbing and working out. I'm very good at it.”

“Is that an accomplishment?”

“Then what do you do for fun, old man?”

“There's this place in Brooklyn, Tommy's. Has the best hot dogs.”

“Hot dogs? I don't even get a burger?”

“If you're good I might even get you a pretzel.”

There it was. Ian had a date with a real estate developer who was taking him to Brooklyn for hot dogs. He called another of his best friends, Charlie York. He was a romantic idealist if Ian ever met one. He was constantly on the search for the One and obsessed with one day obtaining the perfect family; the complete antithesis of Sam. He was also a snobbish, uptight WASP but some things could not be helped.

“He's taking you to get hot dogs?” Charlie asks critically.

“At eleven. He's picking me up,” Ian told him, laying on his bed. “It's all happening very fast.”

“Hot dogs? He's supposed to be trying to sweep you off his feet.”

“You think?”

“Duh. First date equals first impression. This just seems... cheap.”

“According to Sam, he's new money.”

“That explains it. He's probably afraid of being broke again.”

“Hanging up now.”

“Just make sure not to sleep with him.”

“Why not?” Ian asks because he's dying to get this guy under him. 

“You don't put out for hot dogs, Ian. You don't put out for anything less than filet mignon.”

Long after Ian hung up with Charlie, he couldn't help but wonder if his friend was right. In this day and age of sexual liberation, did we still have to earn sex?

Ian couldn't say Mickey lacked style. He picked him up in a sleek town car out of a Turner Classic Movie. Ian walked out of his building, making sure to hurry out of the freezing New York air. The Big Apple had nothing on Chicago when it came to weather, but it was still hard not to get chilled.

Before Ian could touch the handle, the door opened with a grinning Mickey on the other side of it. 

“Get in.”

Ian followed directions well enough. It was more spacious than it appeared on the outside, plenty of leg room. There was a partition raised so Ian could only see the silhouette of a driver. He turned to his date, who was tapping up a final email before he slid his phone into his pocket. 

“Sorry,” he apologizes. “These fucking city guys are dragging their feet on the permits. Condos pop up in New York like fucking McDonald's, yet I'm the only fucker who has to wait six goddamn months for approval.”

“It's fine,” Ian tells him. “My job doesn't exactly keep regular work hours either.”

“You an escort or some shit because I didn't bring cash.”

Ian, not being able to totally tell if Mickey was kidding or not, spotted an issue of New York Today on the floor, along with several other magazine and newspapers, and picked it up, flipping to the Lifestyle section. There was Ian's picture with his accompanying column 'Sex and the Single Guy' and a subtitle 'The Flipper'. He gave it to Mickey who scanned the article, eyes lighting up with laughter. When he finished, he turned to Ian, holding up the magazine.

“You got paid for shit like this?” he wanted to know.

“Pretty damn well for a writer,” Ian glows. “You like it?”

“It's funny. You didn't strike me as funny, Gallagher.”

“Really?”

“You looked smart enough, a bit campy—”

“I'm not fucking campy.”

“— and sexy.”

Ian opens his mouth to reply but finds himself to come up with a reply. Not with the way Ian's looking at him; biting on his bottom lip, his hazy blue eyes raking over Ian. 

They reach for each other at the same time. Mickey drops the magazine and Ian reaches out to clutch his shirt. Their mouths meet somewhere in the middle. One of Ian's hands goes up to fish in the brunet's hair while the other snaked around his neck to pull him closer. Their mouths open and soon Ian was pushing him tongue against Mickey's. The brunet tries his best to move over Mickey who pulled back to nod toward Mickey's driver.

“He's right there,” Ian says breathlessly. 

“He can't hear us,” Mickey reassures before pulling Ian back in for another kiss.

This time, he succeeds in getting himself above Ian who reclines against the door. He trails a hand over the redhead's chest before pulling Ian's shirt above his head. Ian returns the favor by unbuttoning Mickey's shirt and slipping it off along with the white undershirt. He rocks slowly underneath Mickey as he does away with the belt and unzips his slacks. He slips a hand underneath and palms him through the boxers. Mickey rocks in his hand, soft grunts escaping him. He leans down to kiss along Ian's jaw, his neck, before biting into Ian's shoulder when he squeezes him just a bit too hard. 

He looks up at Ian and both of them reach a mutual agreement without uttering a word. They break apart only for them to discard the rest of their clothes. When they're both naked, Mickey pulls Ian down above him for another searing kiss. The redhead rocks him against him tortuously, a wicked grin splitting his face. He wraps his hand around Mickey's cock and begins to move it back and forth slowly. Ian's hand covering him almost more than Mickey can take and he can barely choke out,

“My stuff... pants.”

Ian reaches down with his free arm, blinding searching for Mickey's pants. He lets go Mickey, ignoring his groan of frustration, before fishing out a travel sized bottle of lube and a condom... Trojan, size large. 

“You remembered,” Ian says softly.

Mickey rolls his eyes at the sentiment. “I need you in me all ready.”

So Mr. Big Shot likes to bottom? Ian would be more than happy to oblige. He palms Mickey's ass appreciatively before slicking a finger with the lube and inserting one into the brunet tentatively. He moaned his appreciation but Ian could tell it wasn't enough. He followed it with another and the groan he coaxed from Mickey was so loud, he glanced nervously at the driver who was, thankfully, focused on the road. Just to be sure though, Ian kissed Mickey as he slipped in a third finger to swallow his moan. The brunet moved against his hand, allowing himself to be stretched. He rocked against Ian's hands for awhile before pulling his mouth away.

“Ready.”

Ian quickly sheaths himself and lifted Mickey's leg onto his shoulder and eased in, inch by inch before burying himself to the hilt. After taking a moment to adjust, Ian began to move slowly, one foot on the floor of the car to brace himself while he rocked into Mickey, trying to make the most of the cramped space. Mickey wrapped his free leg around Ian's waist, helping him establish a rhythm. Ian moves in measured strokes at first, using one hand to hold Mickey's foot in place while the other grips his hip. Eventually, his control begins to slip and it all becomes too much; the momentum of the car around them, the little grunts and moans Mickey's making under him. The brunet's eyes are closed, his fingers spasmodically closing into fists before opening again. He was moving almost lazily, barely meeting Ian's thrust.

Abruptly, Ian positioned them so Mickey was straddling him him. The brunet opened his eyes resulting in electric eye contact between the two. It was almost more than either of them could stand. Mickey moved around in short increments, his grip around Ian tightening when he found what he was looking for. Taking the hint, Ian rocks against that particular spot mercilessly. The change in Mickey is almost comedic; he's rocking against Ian almost frantically, eyes rolling back when Ian wraps around his leaking cock. It doesn't take long for him to finish in the redhead's hand. Ian follows him over and slumped back against the seat.

It wasn't a bad hot dog. Ian has his charred, extra relish. Mickey got the works. They eat on the a park bench overlooking the Hudson.

“Isn't it a great dog?" Mickey jabs Ian with his elbow.

“I've had better,” Ian smiles.

“You okay, man?” 

Ian turned to him, a small smile on his lips. “Exhausted. You live in Brooklyn?”

“Nah, I got a place in the Meatpacking District—”

“Very hip.”

“—And I found this place when I was just wandering around one night. Reminded me of home, a little.”

“This city's so huge. It's good to stay grounded.”

They eat the rest of their hot dogs in silence. Ian could imagine how they looked, rumpled clothes half fastened, ruined hair, slightly sweaty, eating hot dogs well past midnight. Then again, it was New York City – how out of place could they look?

**Author's Note:**

> [Follow me on Tumblr](http://harsleywrites.tumblr.com/)


End file.
